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Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19

Our top choices for Pittsfield hotels with a bar

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is NT$4,064
NT$4,539 total
includes taxes & fees
Jul 6 - Jul 7
The Yankee Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (110 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is NT$3,594
NT$3,989 total
includes taxes & fees
Jul 6 - Jul 7
Gregory House Country Inn
Gazebo

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (922 reviews)
"Very clean! Friendly staff! Will stop there again!"
United States
Theresa
The price is NT$2,817
NT$3,311 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Corner Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
"The property was nice and the staff enthusiastic"
United States
Matt
The price is NT$3,005
NT$3,356 total
includes taxes & fees
Jul 12 - Jul 13
Willows Motel Williamstown
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is NT$5,327
NT$5,951 total
includes taxes & fees
Jul 7 - Jul 8
Berkshires Untold
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is NT$4,859
NT$5,442 total
includes taxes & fees
Jul 9 - Jul 10
Little Cat Lodge
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is NT$4,136
NT$4,759 total
includes taxes & fees
Jul 8 - Jul 9
The Cornell Inn, Lenox & The Berkshires
Miscellaneous

1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (451 reviews)
"Older strip type motel. That said room was clean and bed was comfortable. It was good for a couple of days that I stayed. No breakfast available at motel though they did give me a discount coupon to bar/resturant next door. "
United States
William
The price is NT$3,394
NT$3,791 total
includes taxes & fees
Jul 7 - Jul 8
1896 House Country Inn & Motels
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is NT$5,648
NT$7,736 total
includes taxes & fees
Jul 22 - Jul 23
The Red Lion Inn
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (28 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is NT$6,485
NT$7,244 total
includes taxes & fees
Jul 19 - Jul 20
Element by Marriott Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The staff were wonderful! Carli at the front desk was so sweet and went above and beyond! It was fully booked however it still did not seem too crowded at the pool. The outdoor pool is great love that it is salt water. It does open one hour after the indoor pool and close an hour before the indoor pool. But it's great that you have both options. There are plenty of towels provided at the pool for you. It was great having a kitchen to cook breakfast in good variety of supplies. Also really enjoyed the whirlpool tub in the bathroom. The deck with a scenic view off the bedroom was peaceful and beautiful. Great size for our family with two kids the kids slept in the living room and it was nice to have a separate bedroom. There is a movie theater that plays movies at 1pm and 7 pm. DVDs you can check out from the front desk. Activities you can participate in. A coffee bar every morning from 6am to 11 am. Wonderful amenities in a beautiful mountain retreat! The bear by towns have plenty of great places to eat, as well as a pizza place that has much more then pizza that actually delivers all the way up there from Pittsfield."
Autumn 4-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 72 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Hotel On North: Enjoy the bar, free WiFi, and free parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Barrington Stage Company, and then find a cozy spot for a nightcap. Other places to see include Bousquet Ski Area and Hancock Shaker Village. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.

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